


Coming Out on Top

by AnnaNocturnal



Series: Requests and Challenges [5]
Category: Supernatural
Genre: Aggression, Bottom Dean Winchester/Top Sam Winchester, Emotional Hurt/Comfort, Hurt/Comfort, M/M, Submission, Violence
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-04
Packaged: 2018-03-21 06:46:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,841
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3682023
Author URL: https://archiveofourown.org/users/AnnaNocturnal/pseuds/AnnaNocturnal
Summary: <blockquote class="userstuff">
              <p>After years of skirting around the issue, Dean and Sam are finally ready to fuck. The problem is, both say they won’t bottom. They agree to fight it out for dominance, and whoever comes out on top, well…tops. Dean thinks he can best Sam. Dean is totally wrong.</p>
            </blockquote>





	1. Part One

**Author's Note:**

> Written for [this prompt](http://spnkink-meme.livejournal.com/90403.html?thread=35690531#t35690531) at the spnkink-meme livejournal community.

If you asked him, Sam couldn’t really tell you exactly when it started, this thing with Dean, with his big brother. It seemed like as long as he was aware of other people in _that_ way, as long as he had been aware of sex, he had been aware of Dean.

But Dean… Dean could tell you the exact day, hour, minute that it began for him. It was October 25, 1998 at 3:08am. He was 20, his little brother 16. It wasn’t unusual for any of the Winchesters to hear the others jerking off; living in each other’s back pockets, in and out of cramped motel rooms made even the most uncomfortable situations strangely normal. Dean blinked at the glowing LED display on the clock, silently cursed Sammy for waking him, and tried to go back to sleep. Business as usual. 

Except this time, when his little brother came, it was _Dean’s_ name that slipped past his lips on a sigh of ecstasy. 

Dean never did manage to get back to sleep that night. His mind turned the situation over and over in his head, wondering at how his relationship with his innocent baby brother had gotten there, to the point that Sam was getting himself off, thinking of Dean. 

What was worse was that Dean wasn’t especially _bothered_ by it. His mind hyper-focused on what he could’ve done to cause this, to make Sammy this way, to cause this short-circuit in the kid’s brain that made _sex_ and _orgasm_ go hand-in-hand with _Dean_. Cause it had to be something he did, something he instilled in his little brother over the years, when he was bringing him up, helping him bathe, dropping him off at his first day of kindergarten and leaning down to press a kiss to the top of the kid’s head, patching up his wounds after particularly nasty hunts, letting him lean against him, curl in as they slept in the Impala, their father in the driver’s seat… 

But like everything else in their strange, chaotic lives, it eventually began to normalize, and Dean noticed the touches between them begin to linger longer, burn hotter. Noticed Sam’s eyes spark with a strange predatory flame when he caught Dean staring too long. 

It was a slow burn, a slow heat-to-a-boil situation, and it was nearly six years before anything really happened. Of course, maybe it would have happened sooner if Sam hadn’t spent four of those years at Stanford, pretending that Dean and John and the whole hunting life didn’t exist; if he hadn’t spent four years pretending that wasn’t him, that he was destined to live some apple pie life with Jess, with his fancy law degree, a mortgaged house in the ‘burbs, and two-point-five kids. 

And then Jess was killed, and Sam was a wreck. Dean remembered holding him tight, stopping him from running back into the apartment building, muttering in his ear that it was too late, that she was gone, that he was sorry, that it would be okay… _it’ll be okay, baby boy_. 

They got back to the motel room that night and Dean watched as Sam sat, curled in on himself, at the table in the corner. He watched as his little brother broke down, sobbing like his soul was trying to punch its way out of his chest. And yeah, they were supposed to be tough—had been raised to show no weakness—and yeah, Dean hated chick-flick moments, but these lapses in their hard exteriors were another thing that had been normalized over the years. Dean had watched it happen with Sam before, and even with John, and there were even a few times that the other two had watched Dean shatter. 

So Dean crossed the room slowly to stand in front of his brother, pausing only a moment before he reached out and wrapped his arms around the younger man, drawing him tight against his chest, and just held him, feeling Sam’s tears slowly saturating his henley. 

“I’m sorry, Sammy.” He muttered the words over and over again, his fingers raking through his brother’s hair the way they had when Sam had been little and sick and Dean would soothe him through the fever. “So sorry, baby boy.” 

And Sam had finally looked up, his heartbreak etched in every line of his face, the fingers of one hand tangled in the soft-worn fabric of Dean’s shirt as the other moved up to close around the back of the older man’s neck, and when he pulled Dean towards him, Dean didn’t resist, meeting his brother’s lips softly, cutting off a shaking, quiet sob and swallowing it down into his own chest to fester. Any pain he could save Sammy from feeling, he’d take that on. 

The kisses they shared that night were long and slow, sweet and unhurried. There was no end game in mind, only comfort shared between blood. And if that wasn’t how the normal world would do it, that was fine. They were Winchesters, and even before all of this shit with Sam and Dean they were a long way from normal. Why should this be any different? It worked, and it was their damned business. 

Dean held Sam through the night, making calming sounds to soothe his little brother any time he woke up to Sam tossing and crying out in the throes of a nightmare, softly promising him again, _it’ll be okay, baby boy_. The next morning when they woke up it was business as usual. They caught wind of a wendigo and there was a sort of unspoken agreement between them that they were in this for good now as they set out. 

But from then on, Sam would crawl into bed with Dean, the way he did when he was little, and Dean would fight off the nightmares, the way he used to. The only difference now was the soft touches of hands on bare skin and lips pressed to each other, trading heat that became slowly but steadily more intense and consuming as the days passed. 

It was a few months before Sam pulled away from him, meeting Dean’s eyes as his hand traveled down the older man’s chest, over his abs, to follow the light dusting of golden hair below the waistband of Dean’s boxers to palm his swollen cock gently. 

“I wanna fuck you, Dean.” The words were muttered against his lips, a gentle request providing a subtle undercurrent to the desperate proclamation. “Let me fuck you.” 

Dean nearly laughed. Not because the idea was ridiculous; hell, he spent half of his time these days thinking about what it would be like to finally get it on with Sam, to work his brother to the edge, watch his face as he came and choked out Dean’s name the way he had all those years ago. No, he nearly laughed because— 

“I don’t bottom for anyone, Sammy.” He smirked as his brother’s eyes darkened. 

“You’ll bottom for me.” The statement was a dark promise that _almost_ tempted the older man. Almost. 

“I’ll be damned if I’m gonna let my _baby brother_ make me his bitch,” Dean snarled, taking advantage of the fact that his sudden aggression had clearly caught Sam off-guard to roll them over so that Sam was beneath him, landing with his legs splayed, Dean nestled between them, their hard lengths pushed together. Dean let out a hissing exhale at the pleasure the contact sent coursing through him. “I’ll make it good for you, though. Make you come so hard on my cock that you can’t remember your own name.” 

Before he knew what was happening, his little brother was arching his back hard, planting his feet on the bed and then moving hard to toss Dean off of him. The older hunter went tumbling off of the bed, upper body first, the impact with the floor on his back and shoulders knocking the air out of him. He blinked at Sam, dazed as he tried to make sense of what just happened. 

“So that’s how we’re gonna settle this, huh, baby boy?” A grin spread slowly across his face as he picked himself up, taking a stance that gave him a lower center of gravity as his brother stood up, stalking towards him. “Same old rules? Remember, I always kicked your ass.” 

“Times have changed, Dean.” His little brother smirked as Dean’s eyes traveled over his broad shoulders and along the rest of his body, all long, lean muscle. “This time, I’m gonna kick your ass. And then,” he stepped closer, mirroring Dean’s stance as they squared off, that predatory glint back in his eyes. “Then, I’m gonna fuck it.” 

Dean rolled his shoulders, excitement coursing through him. This was gonna be too easy. No way his baby brother was going to come out on top…or get to top. Dean had taught the kid everything he knew. He’d never been one-upped by Sam, and it sure as hell wasn’t going to start today. He’d be deep inside Sam, fucking him into oblivion, in under fifteen minutes.


	2. Part Two

Dean took in that cocky, predatory expression on his brother’s face as he sized him up. It had been years since they sparred, the last time being shortly before Sam left for college, and his brother had filled out considerably in the years since. He had already been bigger than Dean then, a good inch taller and twenty pounds heavier with his broad frame. But now he had at least three inches and forty pounds on him, the lean, lithe muscles of his youth giving way to a harder build.

Dean decided his best bet was to use Sammy’s height against him, throw him off-balance, and without another second’s delay he crouched, swinging his right leg out to sweep Sam’s legs out from under him. The taller man came crashing down, but as he fell he caught Dean’s foot, yanking it hard and pulling the hunter onto his back. Dean let out an _oomph_ as the air left his lungs in a rush and kicked out, his foot connecting with Sam’s shoulder to push him away as he scrambled to regain his footing. The blow hardly seemed to phase Sam, though, and in the time it took Dean to get back on his feet, his little brother did the same. 

They were left back where they started, facing each other, maybe a little worse for wear. 

Shit. This may be harder than Dean thought. 

Before he could decide on a new plan of attack, Sam was rushing him, knocking him back into the wall, his forearm coming up to push against Dean’s chest. The kid was tall enough, and strong enough, to easily press that thick arm against his throat, cut off his air, and something about that—coupled with the fact that Sam _didn’t_ made all of the blood in Dean’s body rush south. 

His little brother let out a low growling sort of sound, pressing his body against him, making any movement nearly impossible for Dean. He leaned forward and nipped at the older man’s plump lower lip. “Can’t wait to fuck you, Dean.” 

Sam shifted his weight to turn Dean around and Dean took the opportunity quickly, bringing up his knee first to plant it in Sam’s stomach, pushing him further back, and then planting the sole of his foot at the bottom of his ribs and thrusting out. The movement knocked Dean off-balance slightly, but he recovered his footing as Sam stumbled backwards, the back of his calves hitting the bed and forcing him to fall backward onto it. 

Dean rushed forward, unwilling to allow Sam the time to recover, to orient himself, and climbed on top, pinning the other hunter to the bed with his knees on either side of Sam’s chest. It was the way he would’ve seated himself if he were going to twist his hands in the younger man’s shirt, pull him towards him and just wail on him. 

It didn’t occur to him that it wasn’t the most opportune position for his purposes. Not until Sam pulled that same arch-and-thrust move he had earlier, forcing Dean to put all of his concentration into remaining upright and on the bed, and suddenly Dean was under Sam again. 

“Dammit, Sammy!” His voice was strained as he struggled for breath under Sam’s weight. Sam seemed to have learned his lesson the last time, though, and didn’t let up, didn’t give Dean a chance to maneuver. 

“You can tap out, you know; surrender.” Sam’s breath was hot on Dean’s neck, causing a shudder to run through him. “Gonna feel so good if you just let go.” 

“Not on your life, baby boy.” Dean attempted the maneuver that Sam had used, arching his back and then whipping back, trying to unseat Sam, but Sam was expecting that and all Dean managed to do was rub his dick against Sam’s stomach, a groan ripping from deep in his chest at the sudden rush of pleasure. 

“That’s it, big brother.” Sam’s voice was sweet and placating, almost mocking. “You feel so good under me. Gonna show you just how good I can make you feel.” 

“Fuck you!” Dean spat. Sam’s cockiness was really starting to irk him. 

But Sam just chuckled. “No, sorry. I’m gonna fuck _you_.” 

Dean opened his mouth to bite off a retort, but the words died in his throat as Sam moved down his body, still using his weight to keep Dean’s legs and hips immobilized. Dean considered using his freed torso to twist away, to push Sam off of him, but then his brother was pushing up the bottom of his shirt, his lips and tongue trailing a wet pattern across his ribs and down over his abs, down to the start of the blonde curls that led into the waistband of his boxers. 

“So not fair, baby boy,” Dean bit out on a moan as Sam cupped him through his boxers. 

“ _Fair_ isn’t in the rules, remember?” Sam chuckled and Dean writhed at the warm air that rushed over his lower abdomen, right over the elastic of the boxers. “Whatever it takes.” 

And Dean couldn’t say anything to that. First, because Sam was right. That had always been the rule when they sparred; they were training to take down things that wanted to kill them, for fuck’s sake. There was no “fair play” in survival. The main reason he couldn’t respond, however, was that Sam’s fingers were now hooked in his waistband, tugging at the material. Dean tried to raise his hips, not caring what happened next with Sam’s face so close to his throbbing dick, but Sam’s weight still pinned him down. 

“Gonna be good for me if I move to take these off?” 

Dean nodded, pushing at Sam’s shoulders to urge him on. He didn’t even care at this point what was going to happen later, not when he was so close to feeling Sam’s mouth on him. Or, he hoped that was what the younger man was planning on doing. 

And hell, maybe after Sam sucked him, got him close, he could take him by surprise, push him off, and get his younger brother under him. Work him open, fuck him hard. 

Yeah, that would work for Dean. 

So when Sam pulled his weight off of him, his eyes wary, Dean “behaved”, lifting his hips off of the bed to let Sam pull his boxers down and then off. He reached down, grasping his dick and running his hand over it slowly, watching Sam’s eyes darken as his tongue flicked out to moisten his lips. 

“Dean…” Sam’s voice was tight as he watched his older brother stroke himself. “Shit…” 

Dean sat up, noting the way Sam went on-edge as he moved. He reached out and pulled his little brother towards him to meet his lips in a sloppy, wet kiss. He pulled back, his lips still touching Sam’s, just barely. He knew what his voice could do to Sam, knew it from the way his brother would shift uncomfortably when he was younger and Dean would tell him about the girls he had bedded, sparing no filthy detail just to see Sammy squirm. 

“Suck me, baby boy.” He let his voice drop to a low rumble, his lips brushing Sam’s as they moved. “Need to feel your hot, wet mouth on my cock before you fuck me.” 

The words, whether Dean had any intention of letting Sam follow through or not, had the desired effect. Sam’s head fell forward as he stifled a groan against Dean’s shoulder, his hips giving an involuntary thrust into the air at the thought. Dean smirked, laying back once more, and Sam followed, bracing himself on his hands as he hovered over his brother. 

Sam leaned down, brushing his lips across Dean’s collar bones and down the center of his chest, pausing to take one dusky pink nipple in his mouth, swirling his tongue over it, teasing it until it was hard, and then biting down gently. Dean moaned, thrusting against his brother’s stomach, seeking any friction he could get as pleasure rushed from his chest straight down to his dick as though the two were wired together. He found himself spreading his thighs further, wanting to wrap them around Sam to find purchase as he ground his dick against him. If he hadn’t been half out of his mind with the rush he would’ve been embarrassed of how wanton he must seem, but as it was he didn’t give a fuck; he needed anything Sam would give him. 

His little brother continued his course down Dean’s body, pausing to dip his tongue in his navel, drawing a breathy moan from Dean as he writhed at the feeling. 

“Stop fucking around.” Dean meant to sound commanding, but to his horror his voice sounded breathless, needy, pleading. 

Sam dragged his tongue along the hard line of muscle that separated Dean’s hip and thigh, bypassing his dick and biting at the vulnerable flesh on the inside of the older man’s thigh. Dean felt the frustration starting to build to the point of bursting inside of him. He was about to give in, to beg, hell, to let Sam fuck him right then and there if that was what it took; anything to get Sam to give him some form of release. 

Before he could open his mouth, however, Sam was moving back up and then his tongue was licking a wide, wet stripe up the underside of Dean’s cock. Dean let out a strangled curse, his head falling back onto the bed, a wet sob of relief nearly escaping him when Sam took the weeping head in his mouth, swirling his tongue around the swollen head and then dipping in the slit, collecting the beaded precum that was forming there. 

“Fuck, Sammy, your mouth is so hot, baby boy, so fucking good…” Dean was rambling, needing to praise what Sam was doing to him, afraid if he didn’t that Sam would stop. 

But Sam only groaned, the vibrations traveling through Dean’s dick and making him arch, trying to thrust up as Sam held his hips in place. He sucked at the tip, swirling his tongue around a few times before he began to sink down, taking more and more of Dean’s hard length into his mouth. 

Dean’s eyes rolled back so fast at the sensation of that wet heat enveloping him that he thought they’d get stuck like that. Even if they did, it would be so worth it. Sam was hollowing out his cheeks, pulling Dean into the back of his throat, sucking hard like he was trying to pull Dean’s very soul out with his cum. Dean felt the head of his dick nudge the back of Sam’s throat, the wet muscles fluttering around the crown as Sam masterfully ignored his gag reflex, rubbing his tongue along the throbbing vein on the underside of the shaft. 

Fuck. Where the hell had Sam learned this? Dean’s mind wandered briefly to the possibility that Sam had been with other guys during his years at Stanford—maybe even before, but at the hot spike of jealous rage that sliced through him he pushed that thought from his head, focusing instead on what his little brother was doing to him now, never mind where he learned it. 

He wasn’t going to last long at this rate, not with Sam masterfully swallowing around him, sucking hard, every now and then pulling back to swirl his tongue around the head, stroking the shaft with his hand as he did so. He needed to act now, if he was going to end up on top. There’d be no point if he came and had to deal with the rebound time before he could actually fuck Sam. 

Maybe he tensed, or went too quiet, seemed too distracted as he considered this, readied himself to act, but Sam seemed to sense what he was planning and he chuckled, sending vibrations through Dean’s dick again, nearly driving him out of his mind before he pulled back, his thumbs rubbing against Dean’s hips as the older man cried out at the loss of heat. 

“Nah, big brother. Not like this.” Sam’s voice was thoroughly fucked out, and before Dean could process the words Sam had flipped him on his stomach. 

As though sensing that Dean would start to fight again if he didn’t do something to stop him, Sam quickly grabbed the firm globes of Dean’s ass, squeezing them with a moan before pulling them apart to see the waiting pucker, quivering in the cool air. Without warning, he dived in, licking slow and wet from right behind Dean’s balls, up over the tight ring of muscles, pausing for only a moment to push his tongue against them, and then continuing up to the top of the cleft. Dean swore as Sam sank his teeth lightly into the sensitive flesh of one check. 

“ _Fuck_ , baby boy.” Dean’s breathing was labored, his voice shaking. “The fuck are you doing to me?” 

“Told you…” Sam smiled against the moist skin and then pressed a kiss to the bite mark before continuing. “Gonna make this so good for you… Gonna work you open with my tongue, fuck you on my fingers until you’re begging for it. Then I’m gonna slide my dick into your pretty virgin ass and fuck you until you shoot your load all over yourself and the bed.” 

Dean groaned. Fuck the plan, fuck topping. He wanted that, wanted everything that Sam was describing. Wanted every filthy word to become action. 

Sam was moving again and Dean’s breath caught in his throat, trying to anticipate where he’d feel him next. He nearly jumped out of his skin when he felt Sam place a soft kiss to his entrance before his tongue came out to swirl around it, bathing the ring of muscles in wet heat. Dean let his forehead fall to the bed, relaxing into Sam’s touch, once more banishing the thought of _where the fuck did Sammy learn this shit_ from his blissed-out mind. His little brother started sucking at his hole, his tongue flicking against the center and Dean nearly shot his wad right then. He dug his fingers into the bedspread and shifted his legs, opening them wider to give Sam easier access. His little brother seemed to take that as a sign, and the next thing Dean knew, that wet muscle was working its way inside him, spearing through the tight ring of muscle, flicking to rub against his inside walls. God it was _so fucking filthy_ , and it was Sam that was doing it to him, and Dean didn’t feel like he’d ever be able to get enough of it even as he felt like it was becoming too much. 

“Sammy…” His voice was a choked sob. “Need to come, baby boy.” 

Sam pulled his mouth away with an obscene slurping sound, and Dean felt one of his fingers pushing gently at his saliva-slicked hole. “Not yet. Want you to come on my cock.” 

Dean let out a low whine, pushing back against the finger that was now dipping past the pucker, working in a bit deeper with each slow, short thrust. 

“That’s it, baby,” Sam muttered, watching Dean begin to fuck himself on his finger. “Doing so good. Can’t wait ‘til it’s my dick inside of you. Should put you in my lap, let you fuck yourself on it, ride me until you come screaming my name.” 

Dean groaned at the image that brought to his mind. “More…please. Sam, just fuck me already.” 

“Shhh...” Sam worked in a second finger, scissoring it and the first, stretching Dean and thrusting slowly. “Don’t want to hurt you.” 

The biting retort that Dean was about to throw out was lost in a long, loud groan as Sam’s fingers brushed a spot inside of him that had him so close to coming he saw sparks and his toes curled. “Fuck, baby boy, right there.” He could just imagine the look on Sam’s face as his brother pressed harder against the spot before adding a third finger and rubbing it, making Dean quake and writhe as he tried to hang on to the last of his control and stave off his orgasm. 

Dean nearly whimpered when the fingers withdrew and then Sam was leaning over him, taking something out of the nightstand. He looked closer, forcing his eyes to focus. It was one of the little bottles of lotion that had been in the bathroom when they arrived at the motel. Dean was confused for a moment and then he heard Sam squirt the lotion into his palm and the wet, sliding sound as he used it to slick his dick up. 

Well, Dean figured it was better than nothing. Hell, Sam had gotten him so worked up that he probably wouldn’t have tried to stop him from going in dry, until it was too late. So points to Sammy for thinking ahead. 

Dean’s breath caught in his throat as he felt the thick head of Sam’s cock come to rest at his entrance, his heart hammering in his chest in anticipation and excitement. 

“Deep breath, Dean,” Sam said softly and then he was pushing inside, slowly but steadily, and Dean tried to do what he said but _god_ it hurt. He felt too full, too stretched, like he was about to rip in half, torn from the inside out by his brother’s dick. 

“Sammy, I don’t think—” Dean’s protests were cut short by a soothing noise from Sam. He was all the way inside now, not moving, his hand rubbing Dean’s lower back in a soothing motion. 

“Doing so good, Dean. So good for me. Just relax…it’ll get better in a minute.” 

Well, Dean sincerely doubted that. But sure enough, after a few moments he could feel his muscles starting to adjust, loosening to accommodate Sam’s length inside of him. He shifted his hips experimentally, nearly bucking in pleasure when he found that Sam was pressed against that spot inside of him. 

“Move…” Dean groaned. “Please.” 

“What was that?” Sam asked, his voice taunting. 

Dean let out a low growl. “ _Please fuck me, Sam!_ You happy? Please, fuck me hard, shove your huge cock so deep in me that I nearly choke on it. Split me open and fucking make me come!” 

Sam cursed, Dean’s words working him up despite the sarcastic tone, and he pulled almost all the way out before snapping his hips forward to bottom out once more. Dean cried out, pushing back against him, arching his back, and in that way they worked up to a desperate rhythm that had them both hanging at the edge after only a few minutes. 

“Dean… Can’t hold on much longer. Need you…need you to come, baby.” Sam’s breathing was labored, words choked out in erratic bursts. 

Dean reached down, balancing on one arm as he fisted his dick, stripping it quickly in time with Sam’s thrusts, and within seconds he felt his balls drawing up against his body, that low hum of pleasure coursing through him, and then complete, soaring relief as he came hard, his vision whiting out as his cum painted the bedspread beneath him in pearly streaks. 

He heard Sam let out a string of curses behind him, not all of them in English, and then his little brother was slamming into him, deeper than before, his hips jerking as he came deep inside Dean. 

When the aftershocks finally subsided for both of them they collapsed, breathing hard, their limbs tangled together. 

After a moment Dean spoke. “Pretty good, Sammy.” He heard his brother let out a low chuckle at the understatement. “Hope you enjoy it that much next time, when I fuck you.” 

Sam sat up, grinning at his older brother. “Fight you for it.”

**Author's Note:**

> Hey guys! This story now has a sequel! Check it out: 
> 
> "Out from Under"  
> [LiveJournal](http://girlgotagun.livejournal.com/15788.html)  
> [AO3](http://archiveofourown.org/works/3713713)  
> 


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